Methanol → Methyl 4-methyl-1,2,3-thiadiazole-5-carboxylate

HRID 392921

Reaction equation

HRID 392921 reaction equation
[CH3:1][C:2]1[N:3]=[N:4][S:5][C:6]=1[C:7]([OH:9])=[O:8].OS(O)(=O)=O.[CH3:15]O>>[CH3:15][O:8][C:7]([C:6]1[S:5][N:4]=[N:3][C:2]=1[CH3:1])=[O:9]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 13819924-Methyl-1,2,3-thiadiazole-5-carboxylic acid

Product 1

HCID 7576666Methyl 4-methyl-1,2,3-thiadiazole-5-carboxylate

Procedure

4-Methyl-[1,2,3]thiadiazole-5-carboxylic acid (1.0 g, 6.94 mmol), concentrated H2SO4 (866 μL), and methanol (12 mL) were combined and heated to reflux for 15 h. The solvent was reduced by a rotary evaporator and the residue was poured into 15 g of ice. The reaction was neutralized with saturated aqueous NaHCO3. The solution was then extracted with CH2Cl2 (4×35 mL). The combined organics were dried over MgSO4, filtered, and concentrated on the rotary evaporator. The product was preadsorbed onto silica gel and purified by flash chromatography to afford the title compound as a yellow oil.

Workup

  1. temperatureheated
  2. temperatureto reflux for 15 h
  3. customThe solvent was reduced by a rotary evaporator
  4. additionthe residue was poured into 15 g of ice
  5. extractionThe solution was then extracted with CH2Cl2 (4×35 mL)
  6. dry with materialThe combined organics were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated on the rotary evaporator
  9. custompurified by flash chromatography

Sources & evidence

ORD record
ord-00f0650f7be147d78a288b0cb1e0715d
Source dataset
uspto-grants-2004_10
Patent number
US06803457B1

Linked notes

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